


Supernatural One Shot Collection

by CloudrunnersCinnamon



Category: Supernatural
Genre: Big Brothers, Caring Dean, Dean Winchester and Feelings, Drabble, Drabble Collection, Drunk Dean, Drunk Dean Winchester, Drunk Winchesters (Supernatural), F/M, FBI Agent Dean Winchester, FBI Agent Sam Winchester, Fluff and Angst, Friendship/Love, Green Eyes, Human Castiel, Hunters & Hunting, Hurt/Comfort, Injured Dean, Little Sisters, One Shot, Other, Protective Castiel, Reader-Insert, Short One Shot, Sick Dean Winchester, Sick Sam Winchester, Supernatural Elements, best friend - Freeform, supernatural imagines
Language: English
Status: In-Progress
Published: 2018-01-03
Updated: 2018-02-18
Packaged: 2019-02-27 21:08:05
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 6
Words: 2,920
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/13256646
Author URL: https://archiveofourown.org/users/CloudrunnersCinnamon/pseuds/CloudrunnersCinnamon
Summary: This work of mine is a Collection of many different one shots and imagines concerning the Winchester Brothers and the people close to them. Some stories are light and funny others are just on the edge of rotting your teeth because there might just be a tiny bit too much fluff and sweetness and some are very dark.The stories are almost always written as a reader insert because that is just how I like to write right now. I will keep updating this collection so stay tuned for updates ;)





	1. Wrap yourself around me

**Author's Note:**

> This Collection is my first attempt on actually going through with posting some of my work. I used to post a lot of it on tumblr but I just find myself gravitating more towards Ao3 so I figured it is about time I post something here :) Anyways I let you get on with reading now and stop rambling.  
> Loads of lovely fandom hugs! <3

\----------------------------------------------------------------------------------------------------------------------------

**Imagine Dean finds you crying in your room.**

\----------------------------------------------------------------------------------------------------------------------------

There is a soft muffled sound coming from (Y/N)’s room, Dean notices while walking past her door and stops in his track. He all so lightly tilts his head towards (Y/N)’s door. Seconds later Dean’s heart is thumping wildly in his chest. (Y/N) is crying – all alone in her room in the secrecy of the depth of the night.

Hesitating, Dean wants to knock before entering the room but he changes his mind and simply pushes down the door handle.  
Almost instantly the crying stops and the lamp on the night table is turned off. Dean walks into the room, quietly, making his way over to (Y/N). She is not making a sound nor is she moving. However they both know, she is just pretending to be asleep and Dean plays along.  
He does not say a word nor does he turn the light back on. Without thinking about it, he gently pulls at the covers and slips under them. Dean waits for a bit to see if (Y/N) still won’t „wake up“ – nothing.

She stays turned around, her back towards Dean. The Winchester moves around a little, putting himself into a comfortable position. He starts to doubt his way of action a little. Sure (Y/N) and him are close but are they that close? Are they „lets lie in bed together“ - close?  
Mentally pushing off all his doubts, Dean slides closer towards (Y/N). He drapes his arms around (Y/N)’s body and pulls her into a warm and comforting embrace.  
The way (Y/N) relaxes into Dean’s hug tells him that he made the right move.  
Sometimes words aren’t necessary, sometimes when it all seems to fall apart all you really need is someone to hold you tight.  
Dean thinks and sighs into (Y/N)’s hair. They both doze off in a matter of minutes.

**Notes for the Chapter:**

> I hope you enjoyed reading this chapter of my Supernatural One Shot Collection :) Thanks for checking it out! I would love some feedback if you've got the time :) Cheers!


	2. A day off with Sam

**Summary for the Chapter:**

> This time just Sammy and you ...

**Notes for the Chapter:**

> This work of mine is a Collection of many different one shots and imagines concerning the Winchester Brothers and the people close to them. Some stories are light and funny others are just on the edge of rotting your teeth because there might just be a tiny bit too much fluff and sweetness and some are very dark.  
> The stories are almost always written as a reader insert because that is just how I like to write right now. I will keep updating this collection so stay tuned for updates ;)

\-----------------------------------------------------------------------------------------------------------------------

**Imagine having a day off from hunting and you and Sam decide to go out for some coffee.**

\----------------------------------------------------------------------------------------------------------------------

A staming, hot cup of coffee is placed in front of you. You smile at the waitress and watch her walk away from your table.

„The coffee smells amazing“ Sam says and takes a first zip. His face lights up and a content smile appears. You feel like this is one of those moments you should try to brand into your memory, you rarely see Sam as relaxed as he is right now.

Still occupied with his coffee Sam doesn‘t notice the way you look at him, how you soak up every tiny little detail. Your hands are wrapped around your cup but for some reason you can‘t bring yourself to look away. Sam‘s eyes are closed and he takes another zip humming softly.

And suddenly it hits you: No way! No way, I can‘t - wait really? He is my best friend, for god‘s sake, and I am in love with him. Noooo!

While you are still struggling with your new epiphany Sam has opened his eyes and flashes you a grin. „How is your coffee, (Y/N)? (Y/N)?“ 

When you don‘t answer Sam looks at you more attentively. Your shoulders are absolutely straight, you are biting on your lower lip and your forehead is in a frown. Definitely the way (Y/N) looks when she is brooding over something, Sam figures.

„(Y/N), what is it? You okay?“ Sam pulls you back from your thoughts. „Uh oh yeah, sorry. I was just thinking about your last hunt. Stupid thoughts!“ You wave it off and try to go back to the way you felt 5 minutes ago. „Okay.“ Sam nods not quite convinced but letting it go for your sake. Gulping down a huge swing of your coffee you smile at Sam from behind the cup.

Shit this is going to be so so exhausting. Your heart picks up a beat...

**Notes for the Chapter:**

> This Collection is my first attempt on actually going through with posting some of my work. I used to post a lot of it on tumblr but I just find myself gravitating more towards Ao3 so I figured it is about time I post something here :) Anyways I let you get on with reading now and stop rambling.  
> Loads of lovely fandom hugs! <3
> 
> I hope you enjoyed reading this chapter of my Supernatural One Shot Collection :) Thanks for checking it out! I would love some feedback if you've got the time :) Cheers!


	3. FBI – kind of cute!

**Summary for the Chapter:**

> Two FBI Agents show up at your work place, questioning every employee about a case. You are never one to be impressed by suits or are you?

**Notes for the Chapter:**

> This work of mine is a Collection of many different one shots and imagines concerning the Winchester Brothers and the people close to them. Some stories are light and funny others are just on the edge of rotting your teeth because there might just be a tiny bit too much fluff and sweetness and some are very dark.  
> The stories are almost always written as a reader insert because that is just how I like to write right now. I will keep updating this collection so stay tuned for updates ;)

\----------------------------

**Imagine going about your job at the bar when two handsome FBI agents show up to question your colleagues and you about some case.**

\----------------------------

When your manager, Stan tells you that you would be up next for the questioning you can’t hide your annoyance. The day was busy enough already and now you had to make room for something you clearly wouldn’t be able to help with. With a little attitude you open the door of the room next to the kitchen and your mood lightens immediately when you realize that – at least they are kind of cute!

The two agents smile at you and invite you to take a seat in front of them. The taller one introduces himself and his partner. His name is Agent Sam Smith and his partner is called Agent Dean Smith, no relation though as he explains.

Dude, I really don’t care, you think, his voice is nice though. You smile to yourself almost unnoticeably.

You try to focus again and listen to what the agents have to say, all the while you study their looks. The agent who hasn’t said anything yet, the smaller one, has short dark blond hair, looks really soft and on his face are what looks like a million freckles. But what really takes your breath and therefore your attention from the other agent are his eyes. They are glistening in every possible shade of green, so it seems and you feel like you have never seen anything as beautiful. The words directed at you sound dull and far away almost like somebody is speaking to you through a thick pillow.

„Ma‘am? (Y/N)?“ Agent Sam Smith waves his hand in front of your face, looking lightly irritated and a bit amused by your behavior. Peeling your eyes off of the short haired man you blush right away. You are embarrassed about getting so distracted and your obvious interest in Agent Dean Smith.

„Uuuhm, sorry agent, I, well, what was the question?“ you flash an apologetic smile and you desperately hope to lose the red on your cheeks. However Dean steps in and begins to speak, „We are wondering, (Y/N) if you had noticed anything weird outside in the parking lot friday night?“ The agent smiles at you and you wonder if you are just imagining the little flirting wink he gives you. You are still fighting with your speechlessness when your head already starts shaking, symbolizing a clear „NO“.

Get a grip already (Y/N), what is wrong with you. You can’t just lose it like this just because you find someone attractive.

After this the interview goes on with a couple more of weird moments, a few more shades of red on your cheeks and now most definitely another flirtatious wink from agent Dean Smith. When the two agents decide all their questions are answered to their satisfaction you are free to leave the room.

With one last, shy glance at the green eyed man you get up – and stumble over your own feet. Great what an elegant exit, good thing I am such a sucker for clumsy looking stunts. Thankful about already facing away from the two agents you blush once more and silently curse under your breath. When the door shuts behind you, you take a deep breath, telling yourself to get over it and putting your head back into work.

Nevertheless your thoughts keep wandering back to the freckled agent every other minute and you just can’t seem to get focused anymore.

30 minutes before your shift is over you finally managed to get a little peace of mind while sorting through the bills from last night. Suddenly you feel someone tapping lightly on your right shoulder. You turn around still looking down on the bills in your hand expecting to see Stan. Your breath catches when you realize that Agent Dean Smith is standing in front of you. His eyes are softer now then they were during the interview and he is grinning. Before you can do or say anything he confidently says, „I heard you are off in half an hour. Fortunately I will be off duty in 10 too, so I thought,“ He shots you another of his breath taking smiles, „so I thought you might like to grab something to eat maybe?“

Finally you were able to gain back your usual quick-wittedness. An elated smile spreads over your face and it is the first time you manage to answer one of the agents questions without hestitation. „I would love that, Agent Smith!“

**Notes for the Chapter:**

> This Collection is my first attempt on actually going through with posting some of my work. I used to post a lot of it on tumblr but I just find myself gravitating more towards Ao3 so I figured it is about time I post something here :) Anyways I let you get on with reading now and stop rambling.Loads of lovely fandom hugs! <3  
> I hope you enjoyed reading this chapter of my Supernatural One Shot Collection :) Thanks for checking it out! I would love some feedback if you've got the time :) Cheers!


	4. Very drunk!

**Summary for the Chapter:**

> You, the reader, are stuck with a very drunk Dean - loads of fun ... maybe XD

**Notes for the Chapter:**

> This work of mine is a Collection of many different one shots and imagines concerning the Winchester Brothers and the people close to them. Some stories are light and funny others are just on the edge of rotting your teeth because there might just be a tiny bit too much fluff and sweetness and some are very dark.  
> The stories are almost always written as a reader insert because that is just how I like to write right now. I will keep updating this collection so stay tuned for updates ;)

\------------------------------------------

**Imagine Dean is drunk and you try to help him get back to the hotel.**

\------------------------------------------

You stumble out of the bar trying to steady a really wonky Dean. He has a sloppy grip on your arm and his upper body and head half rest half flop up and down on your shoulder. Your boots shuffle over the stoney ground and dust keeps getting whirled up.

„Whoops,“ you grab Dean around his waist and almost fall down with him struggling to keep him on his feet.

„Gosh Winchester, how can one be so drunk?“ „Luckily it is really not that far“, you add silently. Dean snakes his arm around your shoulder and reaches out for your hair with his hand. He twirls some of it between his fingers. You start to think he didn’t even notice you were talking to him but then he slurs „I ammm reauuuilly not that druuwank, youuww know.“ His voice is rough from the alcohol and too much karaoke. A whisky breeze hits your nose and you wave your hand to get some fresh air but you still have to cough. „Right,“ cough, „ you are as sober as ever.“

Dean grins and mumbles something incoherently just when he steps into a pothole. The jolting created by Dean’s loss of the rest of his balance takes you down on your left knee and the Winchester lands plain on his butt.

His arm around your shoulder tears you down completely and you fall down next to Dean. After you figure that neither Dean nor you got hurt by the sudden fall an amused laughter escapes your mouth. You slap Dean on his knees and get up. „My mistake Dean, you really aren’t that drunk at all you are absolutely plastered!“

Dean looks up at you, a silly smile on his face. He admittingly nods and holds out a hand to you indicating that you should help him up. You make sure your feet are stable on the ground and grab Dean’s hand. He is already heavy when not drunk but now, all wobbly, you feel like lifting up a hammered baby elephant. But luckily it works and Dean tumbles into you shaking a little but standing up rather straight. For a second he seems to lose his balance again and takes a couple steps backwards but you catch him quickly.

„Woah woah, easy tiger. Let’s walk slowly now, okay?“

Dean takes your hand „yup, leeets doouu that.“

You two manage to go a few meters when suddenly Dean stops walking. He squeezes his eyes weirdly shut and his other hand on your shoulder flops around nervously.

„What is it Dean?“ you start worrying. „Dean?“ No answer. You try to maneuver him around to you and look at him provingly trying to figure out what is wrong. Slowly, Dean lifts up his index finger, symbolizing for you not to interrupt him, „ I thiiiink,“ Dean burps, „ maywwwbe you arrrre right and I have overdone the whisky a litt–„ and before you realize it Dean makes a funny face and a gust of puke hits your shirt.

„NO WAY! DEEEEEAN!“ you have to bite down on your lips to avoid throwing up yourself when the stench hits you. His index finger again… this time he is pointing at your shirt or at his vomit for that matter, „ I hoooope that isn’t ooone of yourrrr favorite shirts (Y/N).“

**Notes for the Chapter:**

> This Collection is my first attempt on actually going through with posting some of my work. I used to post a lot of it on tumblr but I just find myself gravitating more towards Ao3 so I figured it is about time I post something here :) Anyways I let you get on with reading now and stop rambling.Loads of lovely fandom hugs! <3  
> I hope you enjoyed reading this chapter of my Supernatural One Shot Collection :) Thanks for checking it out! I would love some feedback if you've got the time :) Cheers!


	5. Sick days

**Summary for the Chapter:**

> You caught the flu but Dean is taking good care of you.

**Notes for the Chapter:**

> This work of mine is a Collection of many different one shots and imagines concerning the Winchester Brothers and the people close to them. Some stories are light and funny others are just on the edge of rotting your teeth because there might just be a tiny bit too much fluff and sweetness and some are very dark.  
> The stories are almost always written as a reader insert because that is just how I like to write right now. I will keep updating this collection so stay tuned for updates ;)

\------------------------------------------------------

**Imagine you are very sick and Dean is taking care of you.**

\------------------------------------------------------

„Now drink this. It‘ll bring the fever down.“  
Dean hands you a glass of a very thick and brownish looking substance. You wrinkle your nose in disgust.  
Even though your head is pounding and your lungs feel soar from all the coughing you really don‘t think you‘ll be able to down that glass.  
„It looks like throw up, Dean. I can‘t drink this.“ You look at him irritatedly. He just keeps holding the glass right in front of you urging you to take it. You hesitate but when you realize Dean isn‘t taking No for an answer you reluctantly take the drink out of his hand.  
Dean smiles approvingly and gives you a pushing nod communicating a silent go on!  
Obliging him, you take a first careful zip. The liquid runs down your throat and you feel like spitting it all out but you make yourself swallow it quickly.  
„Uuuhh and it also tastes like throw up. Dean what is this?“  
Absolutely disgusted you wipe your mouth with the back of your hand. Determined not to drink anymore of it, you look at Dean with pleading eyes.  
„Please take this,“ you hold up the glass, „or I‘ll be sick!“  
„(Y/N)“ Dean gives it one more try but he can tell you are not just putting on a show. Well okay sweetheart he thinks to himself, I probably wouldn‘t drink it either.

Not really being serious he takes the drink from you and says chuckling, „ you just enjoy getting all the pampering, missy!“  
Falling heavily back on your pillows you pout at Dean.   
„Not true!“  
„Uuhhhhmm,“ Dean responses eye brows raised and leaves the room to get rid of the glass.  
You close your eyes and grin a little. Maybe I am just enjoying it a tiny bit.

**Notes for the Chapter:**

> This Collection is my first attempt on actually going through with posting some of my work. I used to post a lot of it on tumblr but I just find myself gravitating more towards Ao3 so I figured it is about time I post something here :) Anyways I let you get on with reading now and stop rambling.Loads of lovely fandom hugs! <3  
> I hope you enjoyed reading this chapter of my Supernatural One Shot Collection :) Thanks for checking it out! I would love some feedback if you've got the time :) Cheers!


	6. Hello old friend

**Summary for the Chapter:**

> How will Team Free Will handle you while you have that special monthly visitor ...

**Notes for the Chapter:**

> This work of mine is a Collection of many different one shots and imagines concerning the Winchester Brothers and the people close to them. Some stories are light and funny others are just on the edge of rotting your teeth because there might just be a tiny bit too much fluff and sweetness and some are very dark.  
> The stories are almost always written as a reader insert because that is just how I like to write right now. I will keep updating this collection so stay tuned for updates ;)

* * *

 

**Imagine being on your period and all you manage to sense is the hammering pain rushing through you. Surprisingly, Team Free Will does a hell of a job to make you as comfortable as possible and none of the boys shies away because of „lady-stuff“.**

* * *

 

„Oh my god!“ you bend forward pushing your arms into your stomach trying to somehow magically make the pain go away.

Sam sits next to you. His face is plastered with question marks paired with empathy. With his left hand he keeps rubbing your back carefully not to make it worse.

  
„Are you sure I can’t get you anything?“ Cas’s deep voice which is usually very soothing to you during a hunt doesn’t quite have it’s usual effect on you right now. Frustrated, you shake your head and deny his question.  
„Listen (Y/N), my grace is not that low at a level for you to have to go through this. Let me just –„ Cas is already at his feet and the way Sam nods his head at you agreeing silently tells you that they both want you to get better quick. But you aren’t going through this stupid phase of can-I-kill-myself-please for the first time in your life and you know it will only be a couple more hours. Hours which you can gladly endure if it keeps the little grace Cas has left where it should be – right inside of him!

So rather forcefully, to make sure you would bring this discussion to an immediate end, you cut Cas right off.  
„No listen Cas, not the grace thing again okay! I am fine or,“ you roll your eyes,“ I will soon be fine again guys, really!“

You look at them with a serious and confident look in your eyes. They don’t seem to be convinced all the way. „Reeeaaallllyyy!“ You spread the word hoping it emphasizes the meaning behind it.

„Just get me Dean back here with that hot-water bottle, he has been gone for ages.“  
You let yourself fall back against the couch pillows, regretting it instantly - stretched out stomach, not so much fun.

A whimper slips out of your mouth and you roll over to your side. Dammit! So much for calming Sam and Dean down.

„Dean,“ Sam shouts for his brother.  
„What is taking you so long?“  
But before Sam can say another word Dean walks into the room. He is carrying the hot-water bottle and a cup of steaming tea. You smile a little appreciating his mindful thinking. The older Winchester sits himself down on the couch next to you. His gestures and facial expression look a lot more relaxed than Sam’s and Cas’s do and that puts you at ease, too. Even his voice is as steady as ever, „Now, have those two yahoos driven you crazy yet?“ Dean laughs but his brother and Cas don’t even object to his comment. They really are at a loss on how to help you. However Dean confidently pulls your hands away from your stomach. First you want to protest but he quickly replaces them with the hot water bottle and a blanket he places over you. You sigh with relief, the warmth that radiates from the water bottle brings you instant betterment.

As usually when you are on your period you start to get sleepy as soon as you lay down and now is no exception. The sinking pain level lets you drift off into a slumber. Before you are completely gone you mutter something almost incoherently, „Thanks guys - Dean your the best.“ With a smirk on his face Dean turns towards Sam and Castiel.  
„I am the best,“ he makes an innocent face but there is a mischievous twinkling in his eyes, „remember that.“

**Notes for the Chapter:**

> This Collection is my first attempt on actually going through with posting some of my work. I used to post a lot of it on tumblr but I just find myself gravitating more towards Ao3 so I figured it is about time I post something here :) Anyways I let you get on with reading now and stop rambling.Loads of lovely fandom hugs! <3  
> I hope you enjoyed reading this chapter of my Supernatural One Shot Collection :) Thanks for checking it out! I would love some feedback if you've got the time :) Cheers!


End file.
